2,3-Pyridinedicarboxylic acid dimethyl ester Chemical Properties

Melting point:

56°C

Boiling point:

262.3±20.0 °C(Predicted)

Density 

1.231±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Solid

pka

-0.83±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H9NO4/c1-13-8(11)6-4-3-5-10-7(6)9(12)14-2/h3-5H,1-2H3

InChIKey

YLGIBCYHQZTFQL-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=CC=C1C(OC)=O

CAS DataBase Reference

605-38-9(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Pyridinedicarboxylic acid, dimethyl ester(605-38-9)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2933399990

2,3-Pyridinedicarboxylic acid dimethyl ester Usage And Synthesis

Uses

Dimethyl 2,3-Pyridinedicarboxylate is a reagent in the preparation of diarylcyclopentenopyridines as endothelin receptor antagonists.

Synthesis

2,3-Pyridinedicarboxylic acid (80 g, 0.48 mol) was dissolved in methanol (400 ml) and stirred at room temperature for 30 minutes. Concentrated sulfuric acid (94.1 g, 0.96 mol) was then added slowly dropwise for about 1 hour. The reaction mixture was heated to 60°C and the reaction was stirred overnight. After completion of the reaction, methanol was removed by distillation under reduced pressure. The concentrate was slowly poured into aqueous sodium carbonate solution during which a large amount of gas was produced. The pH was adjusted to 7-8 and extracted with dichloromethane (1000 ml × 2). The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give dimethyl 2,3-pyridinedicarboxylate as a pale yellow solid (89.7 g, 99% purity, 95.8% yield).

References

[1] Patent: CN105566319, 2016, A. Location in patent: Paragraph 0185; 0186; 0187; 0188
[2] Australian Journal of Chemistry, 1984, vol. 37, # 1, p. 87 - 94
[3] Patent: EP3252059, 2017, A1. Location in patent: Paragraph 0686; 0686-0688
[4] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 397 - 404
[5] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 433 - 450

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